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Wheelhouse — Unlimited PTO Jobs

Vacation-rental and short-term-rental revenue-management fintech offering Unlimited PTO globally.

5 day weekUnlimited PTOUnited StatesSmall (11-50)Hybrid Remote

About Wheelhouse

What is Wheelhouse?

Wheelhouse is a fintech platform for the $500B+ flex rental space — building dynamic pricing and revenue management software for short and mid-length stay providers. The product helps operators with 1 to 100,000+ listings earn 20%+ more from their rental properties through dynamic pricing, dynamic sets, performance analytics, market reports, and a Navigator product.

The careers page positions the opportunity strategically: "Wheelhouse's technology is helping enable the convergence of hospitality ($1T annual revenue) & residential real estate (a $265T asset class). Our technology empowers short & mid-length stay operators, who manage single-family homes, apartment buildings, and (in some cases) hotels — a broad & massive addressable market." The vision is direct: "Wheelhouse believes a more flexible & connected world is both inevitable & important, and we build technology to make sure the businesses that enable this lifestyle & society can thrive."

In 2021, Wheelhouse's target customer segment voted the platform "Innovation of the Year" at the Data & Revenue Management conference. In 2022, the company closed a significant funding round with participation from "many of the best tech, travel & real estate investors," and the careers page describes the financial position as "long runway, low burn, and rapidly growing revenue."

Where will I work?

Wheelhouse is remote-first and work-anywhere — the careers page is explicit: "We're a remote-first, work-anywhere, and 'yes - you should make time for that adventure/vacation' company, who believes that 'healthy hustle' is the key to good growth." Open roles are split across the U.S. and EU.

What is the Wheelhouse team like?

Wheelhouse is hiring across 6 active roles spanning Sales (Account Executive US, Commercial Account Executive EU), Customer Success (Onboarding Consultant US, EU Onboarding Consultant — both with revenue management expertise), Engineering (Partnership Support Engineer), and Staff Revenue Manager. The team self-description: "transparent & collaborative, and we strive to set our teammates up for success - both professionally & personally."

The founders are "experienced business & product builders who have founded multiple companies together, know our category extremely well, and recognize how rare/special it is to be perfectly positioned around a big opportunity with a very strong cross-functional team."

Work-Life Balance

Wheelhouse offers Unlimited PTO with the explicit "make time for adventure/vacation" framing. The remote-first, work-anywhere setup combined with "healthy hustle" as the operating philosophy means high autonomy and high accountability.

Perks and Benefits

  • Unlimited PTO — "yes, you should make time for that adventure/vacation"
  • Full medical, dental, and vision benefits for each US employee
  • Fidelity 401(k) available for each US employee
  • Competitive salary + equity (e.g. $105K–$120K base + $175K–$200K OTE for US Account Executive)
  • Extended & Competitive Benefits plan
  • Remote-first, work-anywhere — across US and EU
  • Transparent salary ranges disclosed in every JD

Open Positions

7 jobs